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I've never watched Duck Tales but I presume that a Civil War reenactment uses the Confederate flag in a historical sense. But Kevin and his leech are acting uncomfortable just from the fact that this near-completely innocuous flag is being used at all. And in a cartoon of all things.
Wait, he bought an entire box set of the show last night? Wasn't he complaining about not being able to spay or neuter his cat? It's absurd how much Kevin just wastes his money with zero foresight or regret. I've presumed at this point that Steampunk Penny funds all of Kevin's childish desires for the sake of perpetuating his fetish, identical to Frank Wu and Brianna Wu's relationship where Frank paid for his husband/monster thing's SRS.